Bromotrimethylsilane → HCID 9942900, compound

HRID 1681061Notes

Reaction equation

HRID 1681061 reaction equation
C([O:3][P:4]([CH2:9]/[CH:10]=[CH:11]/[CH2:12][NH:13][C:14]1[C:17](=[O:18])[C:16](=[O:19])[C:15]=1[NH2:20])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCCl>[NH2:20][C:15]1[C:16](=[O:19])[C:17](=[O:18])[C:14]=1[NH:13][CH2:12]/[CH:11]=[CH:10]/[CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86746394HCID 86746394, compound

Product 1

HCID 9942900HCID 9942900, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of [(E)-4-[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)amino]-2-butenyl]phosphonic acid diethyl ester (1.0 g, 3.3 mmol) and bromotrimethylsilane (4.6 mL, 35 mmol) in anhydrous 1,2-dichloroethane (30 mL) under nitrogen was refluxed for 20 minutes and then cooled and evaporated. The residue was dissolved in water (150 mL) and washed with diethyl ether (2×75 mL). The resulting material, upon concentrating the aqueous layer, was recrystallized from methanol in ethyl acetate (final volume=100 mL) to yield [(E)-4-[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)amino]-2-butenyl]phosphonic acid one third hydrate as a yellow solid (0.59 g, 71%, mp 220°-230° C. (dec)); IR (KBr, cm-1): 3280, 3100, 1800, 1640; MS (-FAB): 245 (M-H); 1H NMR (DMSO, 400 MHz): δ 7.47 (br s, 3 NH), 5.63-5.58 (m, 2H), 4.10 (br s, 2H), 2.38 (d of d, J=21 and 6 Hz, 2H).

Workup

  1. temperaturecooled
  2. customevaporated
  3. dissolutionThe residue was dissolved in water (150 mL)
  4. washwashed with diethyl ether (2×75 mL)
  5. concentrationThe resulting material, upon concentrating the aqueous layer
  6. customwas recrystallized from methanol in ethyl acetate (final volume=100 mL)

Sources & evidence

ORD record
ord-c883176f7d3448cc94a020dde1ddd230
Source dataset
uspto-grants-1992_12
Patent number
US05168103

Reaction notes

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